Dyestuff of the pyrazolone series and process of making same.



EMU; REJBER, Oil? EASEL, SWITZERLAND, ASSIGNOR 1'0 SOCIETY 015' CHEMICAL INDUSTRY IN BASLE, or BASEL, swrrznnnann.

JDYJESTUFF OF THE PYRAZOLONE SERIES AND PROCESS 01H MAKING SAME.

lflsttdll.

No Drawing.

To all whom it may concern:

Be it known that I, EMIL Rnena, a citizen of the Swiss Republic, and resident of Basel, Switzerland, have invented new and useful Dyestuffs of the Pyrazolone Series and Processes of Making Same, of which the following is a full, clear, and exact specification.

In the United States Letters Patent No. 1210808, dated January 2, 1917 and No. 1,270,325, dated June 25, 1918, are described new dyestufi's of the pyrazolone series obtained by combining oxydiazocompounds of the aromatic series (diazoderivatives of orthoaminophenol or orthoaminonaphthol or of their substitution products), or the diazoderivatives of anthranilic acid or of its Elli till vphenyl radical.

till

substitution products with pyrazolones of the benzene or naphthalene series, cont ainilng a group hydroxyl in the radical vary. a

I have now found, that the diazoder'ivatives of amins, which are not substituted by a group hydroxyl or carboxyl in the position ortho relatively to the group amino, give dyestuffs capable of being chromated and fast to fulling, potting and light, when they are combined with l-phenyl- 3-methyl-5-pyrazolones containing a' group a hydroxyl and a group carboxyl in the In form of their sodium salts, the new dyestufls are yellow to red powders. soluble in water with eenish-yellow to red colorations. In alco ol they are dilficultly soluble, even when heated,with greenish yellow to orange-red colorations. They dissolve in concentrated sulfuric acid with greenishyellow to violet-red, colorations. =They dye wool in an acid batmgreenish-yellow to tilered tints, which, when chromagd, are only slightly changed in c lor. but becomeeverys Specification of Letters Patent.

yellow.

Patented Dec. 3%, Mlle;

' Applicatlim filed February 15, 1918. Serial No. 217,340.

ble in. alcohol, even when heated, with when subsequently chromated, become fast. to light, washing, fulling and potting. 1

When printed on cotton with chromium mordants, it gives a very fast greenish- Example 2: By combining the diazoderivative of 13.7 parts of meta-aminobenzoie acid with 32 parts of 1(5-sulfo-3-carboxy- 2'-oxy)-phenyl-3-methyl-ti-pyrazolone in a solution made alkaline with sodium carbonate, is obtained a yellow dyestufl which can be salted out and dyes wool pure greenish yellow tints, which become very fast to fullin prlnting it with chromium mordants it gives a very pure, fast, greenish-yellow.

and potting, when chromated. By

Example 3: By substituting in Example 1 l for the 9.3 parts of anilin 16.2 parts of 1-amino-2.fi-dichlorobenzene, a dyestud of analogous properties is obtained.

Example 4: 9.3 parts of anilin are diam tized and the resulting diazoderivatiyepis combined with a solution of 26.9 parts of 1 (5, chlor 3' carboxy 2 oxy) phenyl-3- methyl-fi-pyrazolone, made alkaline with sodium carbonate. By saltin out, thesodium salt of the dyestud is ob ained as a yellow precipitate. It dyes wool in an acid bath, greenish-yellow tints which become fast to fulling and potting, when subsequently chromated. Printed on cotton with chromium acetate, it gives a pure, fast, greenishyellow.

Example 5,: By substituting 13.7 parts of meta-aminobenzoic acid for the 9.3 parts of anilin in Example 4, a yellow dvestulf is obtained, which dyes wool fast greenish-yellow tints and gives also on cotton fast greenishyellow prints. I

Example 6: 13.? parts of para-aminoben zoic acid are diazotized and the resulting diazoderivativeis combined with a solution of 23.5 parts of 1(d-carboxy-3'-ox phenyl-3-methyl-5-pyrazolone, made al xaline with sodium carbonate. The dyestud thus obtained dyes wool in an acid bath fast, when subsequently chrom ated. W

cotton with hromium mordants, it gives a fast gold-yel w.

Example Y: TM I 24. parts of dmmsi 1 .1 (5 sulfo 3 oarboxy methyl-ii-pymzolono o bath tile-red tints beso and potting, when subs When printed. on cotton molvdants it givos fast m.

What I claim is: v 1. The hlfiin dose? 1.

n'mnufacturo of utco lyo Y o I lone series, consisting in oonfiifiuing azoderivative of an 1min hloh is not substituted by a group h orcarboxyi in the position ()l'tho" group amino with 1' pymZoion-e containi and a group omfooxyl phenyl.

As new azodyestufis of t constitute in bile yellow to To i pong or s greenish-yellow to red @0201 soluble in alcohol, oa -on greenish-yellow to o ogl and dissolving in you to Wifih greo11ish-yellow tions, Wool in A radical to flEo-vod sinks which, when chr0- fly ohzmgod in color, and. are particularly with chromium 1noromnufaoturo the v .W; bonzano and I o henol-$411061 x iypyrzm ono, which constiforim of ifs sodium salt :1 yellow v, zu'z-r Lo g;x-oonir b-yellow ov.if1y :oh;,. .o in boiling; alcohol Mobil-yellow oration and solubk: in concenimted :-.o f'mio acid with a orow nisl-x oilow to gold-yoilow oolo'ntion, (Ly-2s wooL 111 on :Eoid M11, greenish-yollow tints boo-inning, when mbsbqnomly chronniiod fast to light, washing 'EuHing and pobiing. and giroi, whom gn'intofi on ootfizon mm inorfantsa, o, pan-o, fast,

Elk i U1 REBER. 

